Confectioners&#39; hard butter prepared by low temperature interesterification



Patented June 1, 1948 UNITED STATES PATENT OFFICE CONFEOTIONERB' HARDBUTTER PREPARED BY LOW TEMPERATURE INTEREBTERIFI- CATION No Drawing.Application November 23, 194.8, Serlal No. 711,840

7 Claims. 09-118) This invention relates to the preparation ofconfectloners hard butter from vegetable oils.

The present application contains matter divided from my copendingapplication Serial No. 628,372, filed November 13, 1945, together withadded disclosure as a continuation-in-part over the disclosure dividedfrom said application. In this copending application I have describedand claimed the employment of my process of low temperatureinteresterification (set forth broadly in my copending applicationSerial No. 562,082, filed November 6, 1944) in the treatment ofglycerides for use in edible fats and have made speclilc reference tothe use of the process in the manufacture of confectioners' hard butter.The present application is designed to describe and claim more fullythis specific application of the process and the products producedthereby.

Confectioners hard butters are employed as the tat ingredient in themanufacture of candy and cocky coatings, icings, and fillings forcandies, cookies and other confections. In candy manufacture, forexample, cocoa butter has long been employed as the naturally occurringconfectioners' hard butter. This fat is characterized by its sharpmelting properties, its quality to break sharply and suddenly, that is,its "snap,'

at 70 F. and slightly above, and its ability to melt rapidly andcompletely at body temperature. However, there exist on the mantel: manyproducts of similar characteristics derived from other fats and oils,particularly tropical nut oils characterized by their high content oicombined C12 and C14 fatty acids, commonly referred to as "oils of thecoconut oil group, and including coconut oil, palm kernel oil, babassuoil, tucum nut oil, and the like. (See Lewkowitsch, "Chemical Technologyand Analysis of Oils, Fats and Waxes," Sixth edition, volume 2, pages500 and 617.)

The customary practice of preparing confectioners' hard butter fromthese vegetable oils includes cooling the oil to promote crystallizationof the higher melting constituents, then subjecting the thus grained oilto hydraulic pressing whereby the liquid and solid constituents areseparated. The solid constituent, consisting predominantly of the highermelting glycerides of the oil, and, in the case of coconut oil.amounting to about nineteen percent of the original charge, maybedirectly converted into edible form by deodorization, or may be firstsubjected to a hydrogenation procedure or admixed with a hard stock suchas substantially completely hydrogenated cottonseed oil to improve itsheat reslstance. This type of processing requires considerable manuallabor, provides only part of the oil as desired product, and isexpensive. Consequently much research has been directed toward thedevelopment 0! improved processes, especially those in which fractionalcrystallization of the oil and separation of the fractions isunnecessary.

It is an obiect oi the present invention to provide an improved processfor the manufacture of confectioners hard butter from vegetable oils ofthe coconut oil group.

A further object is to provide a process for the manufacture ofconfectioners' hard butter from oils of the coconut oil group wherebyexpensive steps of fractionation and separation of the solid and liquidglycerides of the oil are avoided.

A still further object is to derive from an oil of the coconut oil groupa confectioners hard butter which contains substantially all of thefatty constituents of the original oil but which is higher meltingwithout being waxy in the mouth at body temperature, has better snap atF., and is possessed of sharp melting characteristics, i. e. the productmelts completely within a narrow temperature range.

In the practice of the present process, an oil of the coconut oil group,such as coconut oil for example, or a partially hydrogenated derivativeof same is subjected to the low temperature interesterification processmore fully set forth in my copending application Serial No. 562,062.This process is based on the discovery that under the proper conditionsof treatment rearrangement of fatty acid radicals of the oil may bedirected and controlled to achieve results not heretofore obtained. Forexample, if the oil of the coconut oil group. at least a substantialpart of which is liquid, is admixed with a suitable catalyst andinteresterification is permitted to take place at a temperature belowthat at which the liquid phase is saturated with respect to relativelyhigh melting triglycerides formed in the course of the interchange offatty acid radicals will crystallize from the liquid fat and take nofurther part in the interchange process. Thus, as molecules having lowsolubility in the liquid lat phase are formed and crystallize out ofsolution, further rearrangement of such molecules is prevented.Consequently the percentage of higher melting molecules in the whole fatmixture tends to increase as long as crystallization continues withresulting increase in melting point. Crystallization of such relativelyinsoluble solid triglycerides can continue as long as the solubilitythereof in the liquid fat phase at the temperature of reaction isexceeded by the amount newly formed in the reaction. After the desiredchange in characteristics has been effected, the oil is preferablyprocessed further by known methods to complete its preparation for usein edible products.

In the application of the low temperature interesterification process tooils such as coconut oil which have a relatively low content of combinedhigh melting fatty acid (e. g. palmitic or stearic acid) and of combinedlow melting fatty acids (e. g. olelc acid or llnoleic acid) the changeeffected in certain physical characteristics, such as increase in spreadbetween initial and complete melting points (American Oil ChemistsSoclety Capillary Method as of Jan. 1, 1944) is not as marked as in thecase of cottonseed oil and soybean oil which contain appreciable amountsof these combined fatty acids. Thus, although the melting point ofcoconut oil, for example, may be raised by the application of lowtemperature interesterification in preparing such fat for use asconfectioners hard butter. the amount of triunsaturated glyceride formedis not sumcient to detract materially from the sharp meltingcharacteristlcs of the higher melting constituents of the fat.Furthermore, the constitution of an oil such as coconut oil is such thatthe glycerides which precipitate during interesterification arepredominantly saturated triglycerides containing more than one kind ofsaturated fatty acid in each molecule (sometimes called "mixedtriglycerides), and such triglycerides, I have found, seem to be moreeffective than triglycerides of a single saturated fatty acid inretaining liquid constituents On crystallization whether mixed in as asolid solution or enmeshed in the crystalline structure. Accordingly.the use of low temperature lnteresteriflcation on oils of the coconutoil group is of outstanding value in the production dried coconut oilhaving a sapouification value of 255.2 and an iodine number of 8.6 wasa81- tated for about hour at 120 F. in a. closed container with 0.3% ofits weight of sodium methoxide in the form of a 10% suspension inxylene. The temperature of the mixture was then Eradually reduced to 70F. and held at that temperature for about one day. Thereafter themixture was further cooled to 60 F. and reaction permitted to take placefor almost five days. At the end of this rearrangement period andwithout substantial change in temperature, the catalyst was inactivatedby the addition of slightly more than an equivalent amount of glacialacetic acid. The oil was then alkali refined. bleached and deodoriaed.Incipient and complete melting points. shown below, were determined bythe closed capillary tube method.

Samples of the processed oil at about 120 F. were Poured into small pansand stored at F. until the samples solidified into small cakes about 2inches by 3 inches by /2 inch. After the samples had reached atemperature of 50 F., they were then stored at 70 F. for at least 16hours. Thereafter the quality of the product to break sharply andsuddenly (snap) was determined by forcing the edge of a knife, spatula,or other similar instrument into the cake of solidifled fat near theedge, noting hardness, and snap of the fat on fracture. Samples of theproduct were also eaten in order to determine edible characteristlcs,such as lack of waxiness, sharpness of fracture during chewing. rapidityof melting. and smoothness during melting at body temperature. Theseresults were compared with results of corresponding examination made onthe original oil and a sample of confectloners' hard butter producedfrom the coconut oil by the customary method of fractionalcrystallization. The superiority of the product of the present inventionis evident from the data shown in the following table.

Incl gags? Eating Characteristics at Body high Point 8 t Temperature e anap a Sample P 1 t.

Smooth- Rapldity of Waxio o ness Melting ness Ori lnal oil w. 5 28. 683. 5 None. Hig meitin fraction obtained by conventional fractionalcrystaliizatlon- 31. 0 32. 5 90. 5 Do.

42.8% of or ginal oil. Whole 011 product from this example 29. 5 32. 790. 8 D

of a higher melting fat with sharp melting char- M acteristics withoutemploying expensive processing steps such as fractional crystallization.

Products of the present invention. accordingly, are characterized by ahigher melting point than the original oil in its natural condition andby a greater concentration of myristic and higher saturated fatty acidsin the higher melting triglyceride components. As the examples belowwill show, such products comprising substantially all of the combinedfatty acids of the original oil, are at least as good as, and by properselection of conditions may be made superior to confectioners hardbutters prepared from the original oil by the conventional methods offractional crystallization and recovery of the solid fraction byhydraulic pressing.

The invention will be more clearly understood from the followingillustrative examples. in which arts are shown by weight. and theaccompanying detailed description.

Example 1.A sample of refined, filtered, and

Example Z.-Reflned, filtered, and dried coconut oll in liquid conditionwas thoroughly mixed with about 0.2% sodium methoxide as a 10%suspension in xylene. The temperature of the mixture was graduallyreduced to a final temperature of 60 F. over a period of several days.Thereafter the catalyst was inactivated by the addition of slightly morethan an equivalent amount of glacial acetic acid, and the product waswashed and filtered. The rearranged coconut oil had sharp meltingcharacteristics, the final melting point being 93.9 F., and hadsufficiently good properties in other respects, such as snap at 70 F.,to serve as a confectioners' hard butter without fractionalcrystallization or hydrogenation. Its characteristics were superior tothose of a product prepared by graining and pressing coconut oil torecover the higher melting components and by adding to this product asmall amount of substantially completely hydrogenated cottonseed oil togive it stability at the higher temperatures.

ammo

In place of the coconut oil. palm kernel oil andbabassuoilorotheroiiofthecoconutoilgroup may be used.

trample 3.A sample of refined and bleached 6 as above described aresatisfactory for use directly as oonfeotioners hard butter, there maysome advantages in subiocting the product of therearrangoment to afractional crystallization palm kernel oil having a saponiiication value3 step whereby desired solid triglycerides are sepof 242.8 and an iodinenumber of 18.0 was chilled stated for use as a confectioners hardbutter. to produce a cloud of solid fat crystals, then Such products areespecially valuable for use warmed slightly until only a light cloud ofcryin the preparation of confections which may meet stals remained. Tothis oil was added 0.3% of with exceptionally high temperatureconditions its weight of sodium methoxide in the form of a duringshipping storage. or sale. In this case, 10% n in xylene. The mixturewas the proportion of solid triglycerides separated is charged to aclosed container adapted to be much higher than that separated from theorigrotated and to effect thereby agitation of the inal oil beforerearrangement. mixture during reaction. The temperature was The finalmelting point alone cannot be used gradually reduced to 70'F. at whichtemperature as a basis for determining the suitability of a the reactionwas allowed to proceed for about product as a confectioners hard butter.Snap one day. The mixture was then further cooled to and eatingqualities are also determining factors. 00 1". and reaction permitted totake place for some products produced by hydrogenation of about 5 days.At the end of the rearrangement coconut oil or of the solid fractionresulting from and without substantial change in temperature, sofractional crystallization thereof, or by the addithe methoxide catalystwas inactivated by the tion' of hard stock such as substantiallycomaddition of slightly more than an equivalent pletely hydrogenatedcottonseed oil to the solid amount of glacial acetic acid. The oil wasthen fraction may have melting points around body alkali refined,bleached, and deodorized. Physical temperature but yet be soft or mushyand lack characteristics were determined as in the case of u snap at 70to 80 F. and therefore be unsuitable Example 1. The results were asfollows: as confectioners hard butters. Of course, as

Complete 3%? ggm snap at Eating at Body sample in 7 a F.

E a" sz m- Rs s ig or V 2 Orl alONO 8.6 25.2 77.3 None Excellent. GoodNone. 11 xneitilljiwgl traction obtained by conventional fractionalcrystaliizatlon- 28.6 30.8 87.4 Fair-good- Good do Do.

".5960! ginal oil.

Wholeoil produotiromthis example 29.2 33 Good ..do .....do Do.

As an auxiliary example, babassu oil may be substituted for palm kerneloil. A product is obtained which is substantially as good as the solidfraction obtained in about 22% yield from the babassu oil byconventional methods of hard butter production involving fractionalcrystalization and separation of liquid and solid fractions.

If it is desired to increase the final melting point of theconfectioners' hard butter as produced in accordance with the aboveexamples, Example 1 for instance, it is possible to accomplish this endby hydrogenatlng the rearranged oil to an iodine value from about one tofive, for example. It is to be understood, however, that the applicationof the hydrogenation step may increase the final melting point of theproduct to such a degree that it may have a waxy consistency and notmelt rapidly or completely at body temperature. Accordingly, thehydrogenation step should preferably be controlled so as to obtain thecharacteristics desired in the final product, more complete saturationbeing desirable for those products designed for use in climates wherethe higher temperatures are encountered.

Higher melting type products may also be made by applying the lowtemperature interesteriiication process to oils of the coconut oil groupwhich have been first hydrogenated. Here also the degree ofhydrogenation is dependent on the characteristics desired in the finalproduct and cannot be set forth with particularity. In the process ofExample 1, for instance, the oil may be partially hydrogenated to aniodine value from about one to about five before interesteriflcation, toproduce higher melting products with greater heat resistance.

Although I have found that products produced above suggested, productsmay be hydrogenated or mixed with sufllcient hard stock to give desiredhardness or snap at such temperatures, but then complete melting doesnot occur at body temperature and the coating, candy, icing, or otherconfection in which the hard stock is used to furnish the fatconstituent may possess a waxiness in the mouth during eating that ishighly undesirable.

In the process above described the temperature at which most fats of thecoconut oil group and their partially hydrogenated derivatives can beginto form solid crystals is below 130 F. and therefore the temperature atwhich the rearrangement is conducted in accordance with this invention,for most practical applications, is below F. but sufficiently high thata substantial proportion of the fat is liquid, and suiliciently low topermit the crystallization from the liquid fat of solid triglyceridefats of low solubility formed in the rearrangement. It has been found,for example, that the reaction will take place at temperatures at whichthe mixture appears to be solid, but actually contains liquid fatentangled in the crystals of precipitated solid glycerides.

In the above examples the maximum final temperature at the completion ofinteresteriflcation is in the neighborhood of 60 F. Lower temperaturesmay be employed such as 40 to 50 F. if it is desirable to increase themelting point of the oil of the coconut oil group above that shown inthe examples. Similarly, temperatures higher than 60 F. may be employedif products of lower final melting point are desired. It will beunderstood. of course, that products obtained by the use of such highertemperatures will not have been rearranged to the same degree as thoseproducts produced at the lower temperatures, and consequently theirphysical properties, including snap at 70' FL, may not be as desirableas those products obtained by processing at lower temperature.

Ordinarily it will be advantageous to reduce the temperature duringinteresteritlcation gradually, or in steps. to the ilna] temperaturedecided upon. However, in some cases it will be preferable to conductthe rearrangement at nearly a constant temperature or at a lowtemperature reached by sudden cooling, or the oil may be seeded, forexample as shown in Example 3 above. My process is not limited to anyset schedule of temperature treatment, although, as indicated, thegradual reduction to the final temperature is preferred.

Efiective practice of the invention does not depend upon the use of anyparticular catalyst. Any material which will promote the interchange offatty acid radicals at the low temperatures required for crystallizationduring interesterlfication is suitable for use.

My copending application Serial No. 628,372 fully discusses the subjectof catalysts and points out that the true catalyst for theinteresteriflcation may be the product of the reaction of thetriglyceride fat and the catalytic material added. Whatever may be thetruecatalyst,itcanbeshown that substances which are effective in bringinabout the interesteriflcation include compounds which include sodium orpotassium for example combined with practically any material less acidicthan phenol. Thus various alkoxides such as sodium, potassium, andlithium methoxides, ethoxides. propoxides and butoxides are suitable, asare alkoxides made from alcoholic compounds in general such as laurylalcohol, ethylene glycol. oleic acid monoglyceride, and many others.Also aikoxides in which the cation is the tetrasubstituted ammoniumradical. such as tetramethyl ammonium methoxide and lauryl benzyldimethyl ammonium methoxide. show activity in promoting thelnteresteriflcation reaction. Other substances which may be added tofurther the interesterification reaction at low temperature are:alkali-metal-organic compounds containing the alkali metal atom directlybound to a carbon atom as in triphenyl methyl sodium, or to 9. nitrogenatom as in potassium pyrrole; finely divided metallic potassium orsodium in xylene; and an anhydrous suspension of potassium hydroxide ina hydrocarbon solvent such as undecane.

Because of the great variety of materials that may be used to form theactive catalyst, and because the actual structure of the true catalyticmaterial is as yet not accurately known, the catalytic materials aregenerically referred to in the claims as "low temperatureinteresterification catalysts."

Amounts of low temperature interesteriflcation catalyst equivalent to0.5 percent by weight of sodium methoxide based on the weight of the fatmay be employed, but there is no particular advantage in employingquantaties much inexcess of 0.3 percent. Even small quantities such as0.03 per cent are effective in promoting the rearrangement at lowtemperature, but I have found that the reaction proceeds at a rather lowrate unless at least 0.05 per cent is employed. My preferred range ofcatalyst usage is the equivalent of from about 0.05 per cent to about0.5 per cent of sodium methoxide.

The catalysts that are used in practicing the present invention arehighly efiicient in eflect- 8 ing regrouping of fatty acid radicals inthe triglycerides, and for this reason it is preferable to render thecatalysts inactive after the desired rearrangement has taken place andbefore the temperature of the fat is allowed to rise appreciably, sothat substantially no modification results during subsequent handling ofthe fat. In order to retain the degree and kind of rearrangementeffected at low temperature, it is preferable to treat the mixturecontaining the catalyst with an acid reacting compound such ashydrochloric acid, phosphoric acid, carbonic acid, glacial acetic acid,etc., and thereby inactivate the catalyst before any undesirablereversion or other change in the desired rearrangement takes place.

In the use of the alkoxide catalysts in the practice oi the invention,the usual precautions of having the oil dry and neutral, the catalystfinely divided and well dispersed, and of excluding oxygen and carbondioxide during the reaction should be observed in order to achieveoptimum results.

Products immediately resulting from the interesteriflcation process maynot be suitable for direct use as an edible product, due to undesirableodor. fatty acid content, or other factors. However, conversion into anedible product may be effected in the customary manner by alkalirefining, filtering or bleaching, and deodorization with steam atelevated temperature under reduced pressure. Thereafter the product isusually panned and chilled, or otherwise converted into cake form orother form suitable for shipping and adapted for use by the customer.

It has been shown above that the products of the present invention havemore snap at temperatures in the neighborhood of F. than do the originaloils from which the products of the present invention are produced andare at least as good in this characteristic as are the products obtainedfrom the original oil by fractional crystallization. It is preferablethat products such as are here concerned possess sharp meltingcharacteristics, that is incipient and complete melting occur over anarrow range of temperature. If incipient melting point determinationsas made by current methods were accurate and reproducible they could bereliably used in conjunction with the final melting points to define andidentify with complete deiiniteness the products of the presentinvention. However, in the absence of a reliable method for thedetermination of the incipient melting point of the fat, the superiorityof products of the present invention is expressed in terms which areindicatlve of the sharp melting charactertistics, that is, snap at atemperature in the neighborhood of 70 F. Thus a product that meltswithin a narrow range near body temperature will likely possess snap at70 F. because all or substantially all of the fat is in solid condition.

Many ways of increasing the melting point of oils of the coconut oilgroup have been tried to make such oils suitable for use asconfectioners hard butter without fractionation or other expensiveprocessing. Thus hydrogenation, ordinary chemical rearrangement in theliquid phase with high melting fats, physical mixing with harder orhigher melting fats, and similar processes have been tried. In allcases, however, the products possess some undesirable characteristicsuch as undesirable softness at temperatures below body temperature,waxiness at body temperature. or lack of snap.

Products of the present invention derived from coconut oil. palm kerneloil and babassu oil, however. have final melting points above 87' I butnot substantially above 100' I and satisfy the requirements of aconfectioners' hard butter in that they are sharp melting. possesssatisfactory snap at 70' It, melt substantially completely at body tem,snd inmanyinstances melt with such rapidity as to give a desirablesensation of cooling during eating. In physical characteristics,therefore, they are superior or equal to those solid products ofsubstantially the same melting point characteristics derived from thesame original oil by fractional crystallization. In addition theproducts are made directly from the whole oil rather than from only asmall traction thereof. the result being a greater supply of a lessexpensive product for the consumer. In the case hydrogenated products orproducts from hydrogenated oils, the same advantages in general willaccrue, except that melting points may he as high as 105115 F. but yetnot so high that the products possess a distinct waxiness at bodytemperatures when eaten.

EiIorts to duplicate products oi the present invention by mixing variousesters of the fatty acids in the correct proportions to give a producthaving the composition of coconut oil or other oil of the coconut oilgroup. and at the same time having the characteristics of the productsproduced by the application of low temperature interesteriiication havenot been successful. An analysis of the conditions existing duringpreparation of the products according to the present invention mayindicate the reason why. In the practice of low temperatureinteresteriflcation on a vegetable oil such as coconut oil for example,the triglycerides which precipitate during reaction and which thereforehave a dominating influence on the characteristics of the final productare not necessarily the highest melting triglycerides which are or canbe formed from the constituent fatty acids in the fat, but ratherglycerldes whose crystallographic properties favored theirprecipitation. Therefore, without knowledge of the kinds and proportionsof triglycerides resulting from practice of low temperatureinteresteriiication on the oil it is impossible to synthesize thecompositions resulting in the practice of this invention. In fact, asfar as I am aware, a satisfactory confectioners' butter has not beenmade directly from the whole oil by any method of synthesis andaccordingly it is my belief that the product is basically new.

Having thus described my invention. What I claim and desire to secure byLetters Patent is:

1. In the process of making a confectioners' hard butter, the stepswhich comprise intimately contacting a glyceride {at of the groupconsisting of oils of the coconut oil group and their hydrogenatedderivatives with a low temperature interesteriflcaticn catalyst at atemperature, below 130 F., at which a substantial portion of the fat isliquid, to cause rearrangement of the fatty acid radicals in the fatmolecules, the temperature being sumciently low to permitcrystallization of solid triglycerides of low solubility as some areformed. maintaining such temperature of the glyceride fat whileprogressive crystallization of solid triglycerides of low solubilitytakes place. inactivating the catalyst and converting the glycei'idemixture into an edible confectioners hard butter.

2. In the process of making a coniectioners hard butter. the steps whichcomprise intimately contacting a glycerlde fat of the group consistingIII 0! oils oi the coconut oil group and their hydrogenated derivativeswith a low temperature interesteriilcation catalyst, at a temperaturebe, low 180' E, at which a substantial portion of the fat is liquid, tocause rearrangement of the i'atti acid radicalsin the fat molecules. thetemperature being sufllciently low to permit crystallization oi solidtriglycerides of low solubility as same are formed. maintaining suchtemperature of the glyceride fat while progressive crystallization ofsolid triglycerides or low solubility takes place and until the completecapillary melting point of the glycerlde fat undergoing rearrangement isabove 87 1. but not substantially above F., inactivating the catalystand convertin the glyceride mixture into an edible coniectioners hardbutter.

3. In the process or making a confectioners' hard butter the steps whichcomprise intimately contacting coconut oil with a low temperatureinteresteriilcation catalyst. at a temperature higher than 50 F. andwithin a temperature range or which the lower limit is the lowesttemperature at which a substantial portion of the fat is liquid and theupper limit is the highest temperature at which solid triglyceridesformed in the reaction can crystallize, maintaining the temperature ofthe glyceride fat at said temperature until the melting point is above87 F., inactivating the catalyst and converting the glyceride mixtureinto an edible coniectioners hard butter.

4. In the process of making a coniectioners' hard butter the steps whichcomprise intimately contacting palm kernel oil with a low temperatureinteresteritlcation catalyst, at a temperature higher than 50 F. andwithin a temperature range of which the lower limit is the lowesttemperature at which a substantial portion of the fat is liquid and theupper limit is the highest temperature at which solid triglyceridesformed in the reaction can crystallize, maintaining the temperature ofthe glyceride fat at said temperature until the melting point is above87 F., inactivating the catalyst and converting the glyceride mixtureinto an edible confectioners hard butter.

5. In the process of making a confectioners' hard butter, the stepswhich comprise intimately contacting a glyceride fat of the coconut oilgroup with a low temperature interesteriflcation catalyst at atemperature, below F., at which a substantial portion of the fat isliquid, to cause rearrangement of the fatty acid radicals in the fatemolecules, the temperature being sufficiently low to permitcrystallization of solid triglycerides of low solubility as same areformed, maintaining such temperature of the glyceride tat whileprogressive crystallization of solid triglycerides of low solubilitytakes place, inactivating the catalyst, hydrogenatlng the rearrangedfat, and converting the resulting glyceride mixture into an edibleconiectioners hard butter.

6. In the process of making a confectioners hard butter, the steps whichcomprise intimately contacting a glyceride fat of the coconut oil groupwith a low temperature interesterification catalyst at a temperature,below 130 F., at which a. substantial portion of the fat is liquid, tocause rearrangement of the fatty acid radicals in the fat molecules, thetemperature being sufllciently low to permit crystallization of solidtriglycerides of low solubility as same are formed, maintaining suchtemperature of the glyceride fat while progressive crystallization ofsolid triglycerides oi low solubility takes place, inactivating thecatalyst, hydrogenating the rearranged fat to an iodine value from aboutone to about five, and converting the resulting glyceride mixture intoan edible contectioners hard butter.

7. As a. product or manufacture suitable for use as a confectioners hardbutter, a fat selected from the group consisting of oils of the coconutoil group and their hydrogenated derivatives, subjected to molecularrearrangement by interesteriflcation in accordance with the process ofclaim 1 and, by reason 01 such molecular rearrangement, having acomplete capillary melting point higher than the original fat but notsubstantially higher than 115 It, the property of breaking sharply andsuddenly at 70 R, which property is at least equal to that 01 a solidfrac- EDDY w. ECKEY.

REFERENCES CITED The following references are of record in the tile 01this patent:

UNITED STATES PATENTS Number Name Date 2,154,452 Jenness Apr. 18, 19392,309,949 Gooding Feb. 2, 1943 Certificate of Correction Patent N 0.2,442,536.

June 1, 1948.

EDDY W. ECKEY It is hereby certified that errors appear in the rintedspecification of the above numbered patent requir' correction asfollows:

olumns 3 and 4, lines 43 to 53,

inclusive, strike out the ta le, and insert the same in Columns 5 and 6,after line 26;

columns 5 and 6, lines 27 to 37, inclusive, strike out the table, and

columns 3 and 4, after line 42 the said Letters Patent shoul insert thesame in column 10, line 55, claim 5, forfate read fat and that d be readwith these corrections therein that the same may conform to the recordof the case in the Patent Ofiice.

Signed and sealed this 17th day of August, A. D. 1948.

THOMAS F. MURPHY,

Am'etcnt Uomme'eeioaer of Patents.

low solubility takes place, inactivating the catalyst, hydrogenating therearranged fat to an iodine value from about one to about five, andconverting the resulting glyceride mixture into an edible contectionershard butter.

7. As a. product or manufacture suitable for use as a confectioners hardbutter, a fat selected from the group consisting of oils of the coconutoil group and their hydrogenated derivatives, subjected to molecularrearrangement by interesteriflcation in accordance with the process ofclaim 1 and, by reason 01 such molecular rearrangement, having acomplete capillary melting point higher than the original fat but notsubstantially higher than 115 It, the property of breaking sharply andsuddenly at 70 R, which property is at least equal to that 01 a solidfrac- EDDY w. ECKEY.

REFERENCES CITED The following references are of record in the tile 01this patent:

UNITED STATES PATENTS Number Name Date 2,154,452 Jenness Apr. 18, 19392,309,949 Gooding Feb. 2, 1943 Certificate of Correction Patent N 0.2,442,536.

June 1, 1948.

EDDY W. ECKEY It is hereby certified that errors appear in the rintedspecification of the above numbered patent requir' correction asfollows:

olumns 3 and 4, lines 43 to 53,

inclusive, strike out the ta le, and insert the same in Columns 5 and 6,after line 26;

columns 5 and 6, lines 27 to 37, inclusive, strike out the table, and

columns 3 and 4, after line 42 the said Letters Patent shoul insert thesame in column 10, line 55, claim 5, forfate read fat and that d be readwith these corrections therein that the same may conform to the recordof the case in the Patent Ofiice.

Signed and sealed this 17th day of August, A. D. 1948.

THOMAS F. MURPHY,

Am'etcnt Uomme'eeioaer of Patents.

